I dig the board game/Mario Partyesque approach to piratin' you got going here!
I'll give it another go trying different choices later on, but my first run ended prematurely: When entering the south-west town on the southern map, the "we've got the next part of the treasure map" cutscene I saw after buying the map in the town on the first map happens again. When I left the town, I came to find my ship nowhere in sight! I might've missed a "robbed by pirates" side quest, but I'm guessing the ship got transported back to map #1. :D Cool, cozy pirate project from what I've seen so far, though!